Chesterfield

Day Trips

Make the most of your day with our curated plans, packed with Chesterfield's hidden gems and unique experiences!

day 1
Exploring Historic Chesterfield
morning
:

Start your day with a visit to the Chesterfield Historical Society to immerse yourself in the rich history of the area. After learning about the local heritage, enjoy a leisurely breakfast at a nearby café, savoring the flavors of the region. Take a stroll through the picturesque streets to admire the charming architecture and quaint shops.

afternoon
:

In the afternoon, head to the Chesterfield Mall for some shopping and entertainment. Browse through a variety of stores or catch a movie at the theater to relax and enjoy some leisure time. Grab lunch at one of the mall's eateries, sampling local cuisine.

evening
:

As the sun sets, make your way to a local restaurant for a delightful dinner that showcases Chesterfield's diverse dining scene. After your meal, consider attending a live performance or local event, which often feature talented musicians and artists. Wind down your evening with a peaceful walk in a nearby park, taking in the serene surroundings.

day 2
Nature Adventures at Babler State Park
morning
:

Kick off your morning with a hearty breakfast before heading to Babler State Park for a day of outdoor adventure. Hike the scenic trails surrounded by nature, breathing in the fresh air as you take in the beauty of the landscape. Make sure to pack a picnic to enjoy mid-hike amid the trees.

afternoon
:

After exploring the trails, spend your afternoon birdwatching or simply relaxing at one of the park's picnic areas. The peaceful ambiance allows you to reconnect with nature while soaking up the sun. Capture the memories with photographs of the lush greenery and various wildlife.

evening
:

Return to Chesterfield for a casual dinner at a local pizzeria famous for its signature pies. Enjoy the laid-back atmosphere and reflect on your day spent in nature. For a sweet ending, stop by a nearby ice cream shop to treat yourself to a delicious dessert.

day 3
Arts and Culture Day
morning
:

Start your day at the Chesterfield Arts Center, where you can participate in or observe local artists at work. Enjoy a light breakfast in the vicinity, fueled by inspiration from the vibrant creative community. Afterward, visit nearby galleries showcasing local artwork.

afternoon
:

In the afternoon, head to the St. Louis Art Museum, which is just a short drive away, to explore its extensive collection of art from around the world. Engage with the exhibits and learn about different cultures through their artistic expressions. Enjoy lunch at the museum café, surrounded by beautiful views of the surrounding park.

evening
:

End your artsy day with a visit to a local theater for a live theater production or concert, providing an opportunity to witness Chesterfield's performing arts scene. After the show, grab dinner at a nearby bistro that offers a blend of local and international flavors. Reflect on the impressive performances as you relish a delightful meal.

day 4
Family Fun at the Carousel
morning
:

Begin your day with breakfast at a family-friendly restaurant before heading to the Chesterfield Township Carousel for a morning of fun. The carousel offers a nostalgic experience for both kids and adults alike, with beautifully crafted animals to ride. Take your time enjoying the carousel, taking photos, and soaking in the cheerful atmosphere.

afternoon
:

After the carousel, visit The Magic House, St. Louis Children’s Museum, where interactive exhibits offer learning opportunities through play. Spend the afternoon immersed in hands-on experiments and engaging activities that spark creativity and curiosity in children. Have lunch at the museum café, picking from kid-friendly options.

evening
:

Wrap up the family day with dinner at a kid-approved restaurant featuring a diverse menu and vibrant ambiance. After dinner, head to a local ice cream shop for dessert, allowing everyone to choose their favorite flavors. Share stories of your fun-filled day and enjoy the laughter together.

day 5
Culinary Exploration
morning
:

Start your day with a culinary class at a local cooking school, where you can learn to prepare some regional specialties. Engage with expert chefs as they guide you through the process, making for an enlightening and delicious experience. Enjoy the fruits of your labor with a tasty breakfast you created yourself.

afternoon
:

In the afternoon, embark on a food tour around Chesterfield, sampling the highlights of the local cuisine at various eateries. Meet local chefs, learn about their cooking philosophies, and enjoy tastings that reflect the community's culinary passions. Don't forget to capture the creative dishes for your food journal.

evening
:

Conclude your culinary adventure at a fine dining restaurant where you can indulge in an exquisite dinner prepared by a renowned chef. Enjoy the artfully crafted meals paired with the perfect wine. Reflect on the flavors and experiences of the day as you wind down in a cozy setting.

day 6
Relaxation Day at the Spa
morning
:

Treat yourself to a serene morning at a local spa where you can indulge in a soothing massage or facial. Start the day with a healthy breakfast at the spa café, setting the tone for rejuvenation and relaxation. Take your time enjoying the tranquil ambiance and pampering treatments.

afternoon
:

After your spa experience, spend the afternoon unwinding at a nearby park or botanical garden, enjoying the beauty of nature. Bring a good book or simply lounge on a bench, letting yourself soak up the calm surroundings. Stop for lunch at a nearby café that offers fresh, healthy options you will love.

evening
:

As the sun begins to set, find your way to a cozy eatery for dinner, where you can enjoy light, refreshing dishes. Share your day of relaxation with friends or family over warm conversations and delicious food. End the day with an evening walk, appreciating the peacefulness of Chesterfield's welcoming environment.

day 7
Shopping and Entertainment Day
morning
:

Start with a breakfast in one of Chesterfield's popular breakfast spots, where you can fuel up for a full day of shopping. After breakfast, head to the Chesterfield Mall to explore a variety of shops including clothing, home goods, and unique boutiques. Don’t forget to check out any special events or pop-ups happening in the mall.

afternoon
:

Continue your shopping spree with a visit to local artisan markets or craft fairs in the area showcasing handcrafted goods. Enjoy lunch at one of the mall’s eateries or a nearby restaurant, soaking in the lively atmosphere. Spend some time browsing through local bookstores or specialty shops for unique finds.

evening
:

Wrap up your busy day with a dining experience at one of Chesterfield's upscale restaurants that offer a delicious menu. After dinner, check out a local theater or comedy club for some entertainment and laughs to conclude the night. Share your favorite finds and experiences with companions as you relax together.

day 8
Sports and Activity Day
morning
:

Kick off your morning with breakfast at a local diner, known for its hearty portions and welcoming vibe. Afterward, head to one of Chesterfield's parks for a leisurely morning of biking or jogging on the scenic trails. Breathe in the fresh air and enjoy the surrounding nature as you get your heart pumping.

afternoon
:

Spend the afternoon at a sports complex where you can engage in various activities such as tennis, basketball, or soccer, either casually or with a group. Have a light lunch in the area or pack a picnic to enjoy afterward. Depending on the season, you might even catch a local game or match in action.

evening
:

Finish the day with dinner at a sports bar where you can watch games on big screens while enjoying classic bar fare. Discuss the day's activities and cheer on your favorite teams with fellow sports enthusiasts. End the night with a leisurely stroll or drive through Chesterfield to unwind.

day 9
Local Parks Exploration
morning
:

Begin your day with breakfast at a local café, fueling up before heading to one of Chesterfield's beautiful parks. Explore the walking trails, taking in the sights and sounds of nature as you ease into your day. Feel free to bring a sketchbook to capture the serene landscapes you encounter.

afternoon
:

Spend your afternoon at another local park, perhaps engaging in group activities like frisbee or a picnic. Enjoy freshly prepared lunch while relaxing in the lush green surroundings. As the day progresses, take your time to Explore the park's amenities, such as playgrounds for children or serene picnic spots.

evening
:

As the evening approaches, find a lovely spot in one of the parks to watch the sunset – the perfect way to conclude a day outdoors. Afterward, enjoy dinner at a nearby restaurant with outdoor seating, allowing you to remain immersed in nature. Reflect on the joy of your day among the beautiful landscapes of Chesterfield.

Discover Chesterfield

Read more in our Chesterfield 2025 Travel Guide.

Chesterfield Travel Guide